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Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum
Hypermonins A-D ( - ), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs ( and ) were isolated and identified from the flowers of . Hypermoins A-D represented the first examples of highly modified...
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| Published in: | Journal of organic chemistry 2021-05, Vol.86 (10), p.7021-7027 |
|---|---|
| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c297t-4a240113ce684ceea57dce8cb0f30c39239154c6678c08b957b86f499e5776d53 |
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| cites | cdi_FETCH-LOGICAL-c297t-4a240113ce684ceea57dce8cb0f30c39239154c6678c08b957b86f499e5776d53 |
| container_end_page | 7027 |
| container_issue | 10 |
| container_start_page | 7021 |
| container_title | Journal of organic chemistry |
| container_volume | 86 |
| creator | Zeng, Yan-Rong Li, Ya-Nan Zhang, Zi-Zhen Hu, Zhan-Xing Gu, Wei Huang, Lie-Jun Li, Yan-Mei Yuan, Chun-Mao Hao, Xiao-Jiang |
| description | Hypermonins A-D (
-
), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (
and
) were isolated and identified from the flowers of
. Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (
-
). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (
) and hyperielliptone HA (
) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil. |
| doi_str_mv | 10.1021/acs.joc.0c02880 |
| format | article |
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-
), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (
and
) were isolated and identified from the flowers of
. Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (
-
). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (
) and hyperielliptone HA (
) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.0c02880</identifier><identifier>PMID: 33881865</identifier><language>eng</language><publisher>United States</publisher><ispartof>Journal of organic chemistry, 2021-05, Vol.86 (10), p.7021-7027</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c297t-4a240113ce684ceea57dce8cb0f30c39239154c6678c08b957b86f499e5776d53</citedby><cites>FETCH-LOGICAL-c297t-4a240113ce684ceea57dce8cb0f30c39239154c6678c08b957b86f499e5776d53</cites><orcidid>0000-0002-3550-161X ; 0000-0001-9496-2152</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33881865$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zeng, Yan-Rong</creatorcontrib><creatorcontrib>Li, Ya-Nan</creatorcontrib><creatorcontrib>Zhang, Zi-Zhen</creatorcontrib><creatorcontrib>Hu, Zhan-Xing</creatorcontrib><creatorcontrib>Gu, Wei</creatorcontrib><creatorcontrib>Huang, Lie-Jun</creatorcontrib><creatorcontrib>Li, Yan-Mei</creatorcontrib><creatorcontrib>Yuan, Chun-Mao</creatorcontrib><creatorcontrib>Hao, Xiao-Jiang</creatorcontrib><title>Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum</title><title>Journal of organic chemistry</title><addtitle>J Org Chem</addtitle><description>Hypermonins A-D (
-
), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (
and
) were isolated and identified from the flowers of
. Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (
-
). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (
) and hyperielliptone HA (
) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNo9kM9LwzAUx4Mobk7P3iRHL93yo0lTb2M6JwwV0XNJs9etI21q0iL9761u-uDx4Mv3fQ4fhK4pmVLC6EybMN07MyWGMKXICRpTwUgkUxKfojEhjEWcST5CFyHsyTBCiHM04lwpqqQYo3LVN-ArV9YBz6P7O_wG2ntdb2GDn52PXp3tGw91b3U7RHPT22ZnnXdb25mydjbgwrsKtzvAS-u-wAfsCvxLLU1X4crVbtvXXXWJzgptA1wd7wR9LB_eF6to_fL4tJivI8PSpI1izWJCKTcgVWwAtEg2BpTJScGJ4SnjKRWxkTJRhqg8FUmuZBGnKYgkkRvBJ-j2wG28--wgtFlVBgPW6hpcFzIm6EAmww7V2aFqvAvBQ5E1vqy07zNKsh-_2eA3G_xmR7_Dx80R3uUVbP77f0L5NwkyeP8</recordid><startdate>20210521</startdate><enddate>20210521</enddate><creator>Zeng, Yan-Rong</creator><creator>Li, Ya-Nan</creator><creator>Zhang, Zi-Zhen</creator><creator>Hu, Zhan-Xing</creator><creator>Gu, Wei</creator><creator>Huang, Lie-Jun</creator><creator>Li, Yan-Mei</creator><creator>Yuan, Chun-Mao</creator><creator>Hao, Xiao-Jiang</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3550-161X</orcidid><orcidid>https://orcid.org/0000-0001-9496-2152</orcidid></search><sort><creationdate>20210521</creationdate><title>Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum</title><author>Zeng, Yan-Rong ; Li, Ya-Nan ; Zhang, Zi-Zhen ; Hu, Zhan-Xing ; Gu, Wei ; Huang, Lie-Jun ; Li, Yan-Mei ; Yuan, Chun-Mao ; Hao, Xiao-Jiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c297t-4a240113ce684ceea57dce8cb0f30c39239154c6678c08b957b86f499e5776d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeng, Yan-Rong</creatorcontrib><creatorcontrib>Li, Ya-Nan</creatorcontrib><creatorcontrib>Zhang, Zi-Zhen</creatorcontrib><creatorcontrib>Hu, Zhan-Xing</creatorcontrib><creatorcontrib>Gu, Wei</creatorcontrib><creatorcontrib>Huang, Lie-Jun</creatorcontrib><creatorcontrib>Li, Yan-Mei</creatorcontrib><creatorcontrib>Yuan, Chun-Mao</creatorcontrib><creatorcontrib>Hao, Xiao-Jiang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeng, Yan-Rong</au><au>Li, Ya-Nan</au><au>Zhang, Zi-Zhen</au><au>Hu, Zhan-Xing</au><au>Gu, Wei</au><au>Huang, Lie-Jun</au><au>Li, Yan-Mei</au><au>Yuan, Chun-Mao</au><au>Hao, Xiao-Jiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J Org Chem</addtitle><date>2021-05-21</date><risdate>2021</risdate><volume>86</volume><issue>10</issue><spage>7021</spage><epage>7027</epage><pages>7021-7027</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Hypermonins A-D (
-
), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (
and
) were isolated and identified from the flowers of
. Hypermoins A-D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (
-
). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (
) and hyperielliptone HA (
) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.</abstract><cop>United States</cop><pmid>33881865</pmid><doi>10.1021/acs.joc.0c02880</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-3550-161X</orcidid><orcidid>https://orcid.org/0000-0001-9496-2152</orcidid></addata></record> |
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| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| title | Hypermoins A-D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum |
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